TW200528512A - Liquid uncrosslinked michael addition oligomers prepared in the presence of a catalyst having both an epoxy moiety and a quaternary salt - Google Patents

Liquid uncrosslinked michael addition oligomers prepared in the presence of a catalyst having both an epoxy moiety and a quaternary salt Download PDF

Info

Publication number: TW200528512A
Authority: TW; Taiwan
Prior art keywords: functionality; precursor; acetate; item; ethyl
Prior art date: 2002-09-26

Application number

TW93104509A

Other languages

English (en)

Chinese (zh)

Inventor

Laurence G Dammann

Michael L Gould

Original Assignee

Ashland Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-09-26

Filing date

2004-02-24

Publication date

2005-09-01

2004-02-24 Application filed by Ashland Inc filed Critical Ashland Inc

2005-09-01 Publication of TW200528512A publication Critical patent/TW200528512A/zh

Links

239000004593 Epoxy Substances 0.000 title claims abstract description 27
150000003839 salts Chemical group 0.000 title claims abstract description 26
239000007788 liquid Substances 0.000 title claims abstract description 20
239000003054 catalyst Substances 0.000 title claims abstract description 17
238000006845 Michael addition reaction Methods 0.000 title abstract 2
239000000203 mixture Substances 0.000 claims abstract description 36
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 78
-1 tritium halide Chemical class 0.000 claims description 55
239000002243 precursor Substances 0.000 claims description 32
238000006243 chemical reaction Methods 0.000 claims description 29
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 23
229920005989 resin Polymers 0.000 claims description 23
239000011347 resin Substances 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
125000004386 diacrylate group Chemical group 0.000 claims description 10
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 9
230000002079 cooperative effect Effects 0.000 claims description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 7
125000000524 functional group Chemical group 0.000 claims description 7
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 7
239000000178 monomer Substances 0.000 claims description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 5
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
238000007259 addition reaction Methods 0.000 claims description 4
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical group CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 3
239000002202 Polyethylene glycol Substances 0.000 claims description 3
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 3
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
150000002118 epoxides Chemical class 0.000 claims description 3
YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 3
229920000728 polyester Polymers 0.000 claims description 3
229920001223 polyethylene glycol Polymers 0.000 claims description 3
ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
NXQNMWHBACKBIG-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCCC(O)(O)O Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCCC(O)(O)O NXQNMWHBACKBIG-UHFFFAOYSA-N 0.000 claims description 2
FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 2
DJACTCNGCHPGOI-UHFFFAOYSA-N butyl 2-cyanoacetate Chemical compound CCCCOC(=O)CC#N DJACTCNGCHPGOI-UHFFFAOYSA-N 0.000 claims description 2
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 claims description 2
ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 claims description 2
229920001610 polycaprolactone Polymers 0.000 claims description 2
239000004632 polycaprolactone Substances 0.000 claims description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims 7
235000009421 Myristica fragrans Nutrition 0.000 claims 5
239000001115 mace Substances 0.000 claims 5
125000002947 alkylene group Chemical group 0.000 claims 3
150000001412 amines Chemical class 0.000 claims 3
PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims 2
LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims 2
INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims 2
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims 2
OYFIDALWMSGYLQ-UHFFFAOYSA-N 2-ethyl-n-phenylbutanamide Chemical compound CCC(CC)C(=O)NC1=CC=CC=C1 OYFIDALWMSGYLQ-UHFFFAOYSA-N 0.000 claims 2
RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims 2
239000005007 epoxy-phenolic resin Substances 0.000 claims 2
MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 claims 2
229910052735 hafnium Inorganic materials 0.000 claims 2
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 2
238000000034 method Methods 0.000 claims 2
MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 claims 2
VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 claims 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 2
229910052722 tritium Inorganic materials 0.000 claims 2
PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 claims 1
KFNABOVSAPCOCY-UHFFFAOYSA-N 1-propanoyloxypropan-2-yl propanoate Chemical compound CCC(=O)OCC(C)OC(=O)CC KFNABOVSAPCOCY-UHFFFAOYSA-N 0.000 claims 1
WYZUHTNYQYXVQX-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;propanoic acid Chemical compound CCC(O)=O.CCC(O)=O.OCC(C)(C)CO WYZUHTNYQYXVQX-UHFFFAOYSA-N 0.000 claims 1
FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims 1
MFESDECRFFWRQI-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl propanoate Chemical compound CCC(=O)OCCOCCO MFESDECRFFWRQI-UHFFFAOYSA-N 0.000 claims 1
MOBRAWLJDOLOGM-UHFFFAOYSA-N 2-(2-methylpropanoylamino)butanamide Chemical compound CCC(C(=O)N)NC(=O)C(C)C MOBRAWLJDOLOGM-UHFFFAOYSA-N 0.000 claims 1
BHEFUPPIKIGXRC-UHFFFAOYSA-N 2-(2-propanoyloxypropoxy)propyl propanoate Chemical compound CCC(=O)OCC(C)OCC(C)OC(=O)CC BHEFUPPIKIGXRC-UHFFFAOYSA-N 0.000 claims 1
YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 claims 1
WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 claims 1
UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 claims 1
VKIGAWAEXPTIOL-UHFFFAOYSA-N 2-hydroxyhexanenitrile Chemical compound CCCCC(O)C#N VKIGAWAEXPTIOL-UHFFFAOYSA-N 0.000 claims 1
UMRLNZREIFILSG-UHFFFAOYSA-N 3-propanoyloxypropyl propanoate Chemical compound CCC(=O)OCCCOC(=O)CC UMRLNZREIFILSG-UHFFFAOYSA-N 0.000 claims 1
ADGOOVVFTLKVKH-UHFFFAOYSA-N 4-propanoyloxybutyl propanoate Chemical compound CCC(=O)OCCCCOC(=O)CC ADGOOVVFTLKVKH-UHFFFAOYSA-N 0.000 claims 1
XAMCLRBWHRRBCN-UHFFFAOYSA-N 5-prop-2-enoyloxypentyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCOC(=O)C=C XAMCLRBWHRRBCN-UHFFFAOYSA-N 0.000 claims 1
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 1
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims 1
VGYPHJFLVYHPJI-UHFFFAOYSA-N C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.CC(C=C)(C)C Chemical compound C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.CC(C=C)(C)C VGYPHJFLVYHPJI-UHFFFAOYSA-N 0.000 claims 1
FJKJHNSSTDEXCR-UHFFFAOYSA-N C(C)C(C(=O)O)(CC)CC.C(O)C(CC)(CO)CO Chemical group C(C)C(C(=O)O)(CC)CC.C(O)C(CC)(CO)CO FJKJHNSSTDEXCR-UHFFFAOYSA-N 0.000 claims 1
SOWHLEQLSPBFTQ-UHFFFAOYSA-N CCC.CCC.CCC.CCC.OCC(CO)(CO)CO Chemical compound CCC.CCC.CCC.CCC.OCC(CO)(CO)CO SOWHLEQLSPBFTQ-UHFFFAOYSA-N 0.000 claims 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
239000004641 Diallyl-phthalate Substances 0.000 claims 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
AOSWRWMLSUAOIP-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.NC1=NC(N)=NC(N)=N1 Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.NC1=NC(N)=NC(N)=N1 AOSWRWMLSUAOIP-UHFFFAOYSA-N 0.000 claims 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 1
ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims 1
HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims 1
FCCCRBDJBTVFSJ-UHFFFAOYSA-N butanehydrazide Chemical compound CCCC(=O)NN FCCCRBDJBTVFSJ-UHFFFAOYSA-N 0.000 claims 1
WKAYRWBOFSKJPB-UHFFFAOYSA-N ethyl carbamate prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCOC(N)=O WKAYRWBOFSKJPB-UHFFFAOYSA-N 0.000 claims 1
TZMFJUDUGYTVRY-UHFFFAOYSA-N ethyl methyl diketone Natural products CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims 1
KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims 1
229920001515 polyalkylene glycol Polymers 0.000 claims 1
229920005650 polypropylene glycol diacrylate Polymers 0.000 claims 1
229920001296 polysiloxane Polymers 0.000 claims 1
ZZPKLSNHENDBHJ-UHFFFAOYSA-N prop-2-enoic acid 1,3,5-triazine-2,4,6-triamine Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.NC1=NC(N)=NC(N)=N1 ZZPKLSNHENDBHJ-UHFFFAOYSA-N 0.000 claims 1
LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims 1
239000011541 reaction mixture Substances 0.000 claims 1
150000004756 silanes Chemical class 0.000 claims 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 abstract description 4
239000000853 adhesive Substances 0.000 abstract description 2
230000001070 adhesive effect Effects 0.000 abstract description 2
229940093499 ethyl acetate Drugs 0.000 description 19
235000019439 ethyl acetate Nutrition 0.000 description 19
239000000047 product Substances 0.000 description 10
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000126 substance Substances 0.000 description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000002904 solvent Substances 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241000981595 Zoysia japonica Species 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl triethylammonium chloride Substances [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
230000004927 fusion Effects 0.000 description 3
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
208000003251 Pruritus Diseases 0.000 description 2
229920002125 Sokalan® Polymers 0.000 description 2
239000002585 base Substances 0.000 description 2
238000010586 diagram Methods 0.000 description 2
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
239000003446 ligand Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
230000005855 radiation Effects 0.000 description 2
239000002994 raw material Substances 0.000 description 2
229910052702 rhenium Inorganic materials 0.000 description 2
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
RLWTYSCBQDVDRW-UHFFFAOYSA-N 2,2-bis(propanoyloxymethyl)butyl propanoate Chemical compound CCC(=O)OCC(CC)(COC(=O)CC)COC(=O)CC RLWTYSCBQDVDRW-UHFFFAOYSA-N 0.000 description 1
KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 1
YHZCIHZXDLETJW-UHFFFAOYSA-N 2-ethenylbut-3-enoic acid Chemical compound OC(=O)C(C=C)C=C YHZCIHZXDLETJW-UHFFFAOYSA-N 0.000 description 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical class OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
RDBNAQJXOYZUFL-UHFFFAOYSA-N 2-methylidenetetradecanoic acid Chemical compound CCCCCCCCCCCCC(=C)C(O)=O RDBNAQJXOYZUFL-UHFFFAOYSA-N 0.000 description 1
XOLJIAGFCWEBOG-UHFFFAOYSA-N 3-oxobutanimidamide Chemical compound CC(=O)CC(N)=N XOLJIAGFCWEBOG-UHFFFAOYSA-N 0.000 description 1
MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
UWSLPNWPRYFAMX-UHFFFAOYSA-N 9h-fluoren-9-yl acetate Chemical compound C1=CC=C2C(OC(=O)C)C3=CC=CC=C3C2=C1 UWSLPNWPRYFAMX-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
OGEQHQKYUNRGJI-UHFFFAOYSA-N O=C(CCOCCOC(C(=C)C)=O)C Chemical compound O=C(CCOCCOC(C(=C)C)=O)C OGEQHQKYUNRGJI-UHFFFAOYSA-N 0.000 description 1
229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241000271570 Rhea americana Species 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
VZWGRQBCURJOMT-UHFFFAOYSA-N acetic acid n-dodecyl ester Natural products CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
229920006397 acrylic thermoplastic Polymers 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
239000008393 encapsulating agent Substances 0.000 description 1
REDWICFTZSAVSL-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O.CCOC(N)=O REDWICFTZSAVSL-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
238000002309 gasification Methods 0.000 description 1
238000001879 gelation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000009434 installation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
230000007803 itching Effects 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
MBCTWXWDQMXVDF-UHFFFAOYSA-N octyl 2-cyanoacetate Chemical compound CCCCCCCCOC(=O)CC#N MBCTWXWDQMXVDF-UHFFFAOYSA-N 0.000 description 1
238000012856 packing Methods 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
WPSRZZSBIXVLRN-UHFFFAOYSA-N prop-1-ene 2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C(C=C)(=O)OC(C)COC(C)COC(C)COC(C=C)=O.C=CC.C=CC WPSRZZSBIXVLRN-UHFFFAOYSA-N 0.000 description 1
AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
239000000565 sealant Substances 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 1
NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/04—Acids, Metal salts or ammonium salts thereof
- C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/13—Morphological aspects
- C08G2261/135—Cross-linked structures
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/76—Post-treatment crosslinking
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Laminated Bodies (AREA)
Macromonomer-Based Addition Polymer (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

TW93104509A 2002-09-26 2004-02-24 Liquid uncrosslinked michael addition oligomers prepared in the presence of a catalyst having both an epoxy moiety and a quaternary salt TW200528512A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US10/255,541 US6706414B1 (en)	2002-09-26	2002-09-26	Liquid uncrosslinked Michael addition oligomers prepared in the presence of a catalyst having both an epoxy moiety and a quaternary salt

Publications (1)

Publication Number	Publication Date
TW200528512A true TW200528512A (en)	2005-09-01

Family

ID=31946508

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW93104509A TW200528512A (en)	2002-09-26	2004-02-24	Liquid uncrosslinked michael addition oligomers prepared in the presence of a catalyst having both an epoxy moiety and a quaternary salt

Country Status (12)

Country	Link
US (1)	US6706414B1 (de)
EP (1)	EP1545876B1 (de)
JP (1)	JP2006501330A (de)
KR (1)	KR20050070006A (de)
CN (1)	CN100377874C (de)
AT (1)	ATE557049T1 (de)
AU (1)	AU2003272716B2 (de)
CA (1)	CA2500205C (de)
ES (1)	ES2384873T3 (de)
MX (1)	MXPA05003246A (de)
TW (1)	TW200528512A (de)
WO (1)	WO2004029118A2 (de)

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KR20070042503A (ko) *	2004-04-21	2007-04-23	앳슈랜드 라이센싱 앤드 인텔렉츄얼 프라퍼티 엘엘씨	내장 광개시제를 갖는 복사-경화성 마이클 부가 수지
US20050245636A1 (en) *	2004-04-29	2005-11-03	Ashland Inc.	Radiation-curable coatings for wood substrates from multifunctional acrylate oligomers
US7317061B2 (en) *	2004-04-29	2008-01-08	Ashland Licensing And Intellectual Property Llc	Self-photoinitiating water-dispersible acrylate ionomers and synthetic methods
US7214725B2 (en) *	2004-04-30	2007-05-08	Ashland Licensing And Intellectual Property Llc	Radiation-curable lithographic inks from multifunctional acrylate oligomers
EP1756035B1 (de) *	2004-05-02	2013-08-14	Ashland Licensing and Intellectual Property LLC	Strahlungshärtbare beschichtungen für metallsubstrate aus multifunktionellen acrylatoligomeren
US7232540B2 (en) *	2004-05-02	2007-06-19	Ashland Licensing And Intellectual Property Llc	Radiation-curable coatings for plastic substrates from multifunctional acrylate oligomers
EP1647588A3 (de) *	2004-10-13	2006-11-02	Rohm and Haas Company	An der Oberfläche aktivierte Michaelhärtung
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US10472446B2 (en) *	2013-03-04	2019-11-12	Toyo Gosei Co., Ltd.	Composition, resin mold, photo imprinting method, method for manufacturing optical element, and method for manufacturing electronic element
BR112015025624B1 (pt)	2013-04-08	2021-09-08	Allnex Netherlands B.V	Composição reticulável, kit, método para preparação de uma composição reticulável, e, composições de revestimento
JP2016537467A (ja) *	2013-11-25	2016-12-01	ダウグローバルテクノロジーズエルエルシー	生分解性脂肪族ポリエステル
EP3283588B1 (de)	2015-04-17	2025-06-18	Allnex Netherlands B.V.	Vernetzbares rma-harz und verwendung in vernetzbaren rma-zusammensetzungen
EP3283583A1 (de)	2015-04-17	2018-02-21	Allnex Netherlands B.V.	Verfahren zur herstellung einer vernetzbaren zusammensetzung
US20180163081A1 (en)	2015-04-17	2018-06-14	Allnex Netherlands B.V.	A rma crosslinkable composition with improved adhesion
WO2016166361A1 (en)	2015-04-17	2016-10-20	Nuplex Resins B.V.	Floor coating compositions
JP7330943B2 (ja) *	2017-07-31	2023-08-22	ダウグローバルテクノロジーズエルエルシー	洗剤添加剤
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2002
- 2002-09-26 US US10/255,541 patent/US6706414B1/en not_active Expired - Lifetime
2003
- 2003-09-26 AT AT03754917T patent/ATE557049T1/de active
- 2003-09-26 CN CNB038254050A patent/CN100377874C/zh not_active Expired - Fee Related
- 2003-09-26 WO PCT/US2003/030436 patent/WO2004029118A2/en not_active Ceased
- 2003-09-26 CA CA2500205A patent/CA2500205C/en not_active Expired - Fee Related
- 2003-09-26 JP JP2004539988A patent/JP2006501330A/ja not_active Ceased
- 2003-09-26 AU AU2003272716A patent/AU2003272716B2/en not_active Ceased
- 2003-09-26 MX MXPA05003246A patent/MXPA05003246A/es active IP Right Grant
- 2003-09-26 ES ES03754917T patent/ES2384873T3/es not_active Expired - Lifetime
- 2003-09-26 EP EP20030754917 patent/EP1545876B1/de not_active Expired - Lifetime
- 2003-09-26 KR KR1020057005203A patent/KR20050070006A/ko not_active Ceased
2004
- 2004-02-24 TW TW93104509A patent/TW200528512A/zh unknown

Also Published As

Publication number	Publication date
EP1545876A2 (de)	2005-06-29
CN100377874C (zh)	2008-04-02
CN1708401A (zh)	2005-12-14
KR20050070006A (ko)	2005-07-05
CA2500205C (en)	2010-07-06
ATE557049T1 (de)	2012-05-15
AU2003272716B2 (en)	2008-02-14
EP1545876A4 (de)	2008-10-01
WO2004029118A3 (en)	2004-06-24
EP1545876B1 (de)	2012-05-09
AU2003272716A1 (en)	2004-04-19
CA2500205A1 (en)	2004-04-08
JP2006501330A (ja)	2006-01-12
WO2004029118A2 (en)	2004-04-08
US6706414B1 (en)	2004-03-16
MXPA05003246A (es)	2005-07-05
ES2384873T3 (es)	2012-07-13

Publication	Publication Date	Title
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